This is a follow-up to the pair of essays I wrote earlier this week. First, I amended the MacLeod organizational hierarchy to include a fourth category, the Technocrat. Secondly, I began to explore different workplace cultures. Now I’m going to extend the three-culture model to include a fourth. Before I do that, let me revisit the assumptions of the first two essays.

The MacLeod Model assigns unflattering labels to the three tiers of the modern corporation. Workers are Losers, managers are Clueless, and executives are Sociopaths. Examining the behaviors associated with each, we get three baseline traits that organizations use to evaluate the quality of its people: subordinacy, dedication, and strategic orientation. Call these traits the “3 S’s” that organizations use to evaluate the quality of its people. If we treat these traits as binary and look at them in combination, we get up to 8 categories of employees:

Subordinacy  Dedication  Strategy  Category           MacLeod destination
False        False       False     Passive            Fired or Lumpenloser
True         False       False     Yes-Person         Lumpenloser
False        True        False     Loose Cannon       Fired or Lumpenloser
True         True        False     Workhorse          Clueless (middle manager)
False        False       True      Passive-Aggressive Highly variable!
True         False       True      Team-Player        Loser (subordinate)
False        True        True      Self-Executive     Sociopath (executive)
True         True        True      Protege            (unclear)


My original analysis focused on the team-players (MacLeod Losers), the workhorses (MacLeod Clueless), and the self-executives (MacLeod Sociopaths, whom I further divided between the “good Sociopath” Technocrats and the toxic Psychopaths). The assumption I held was that an employee with fewer than two of these three assets would not retain employment, while those with all three were a contradiction in terms. On further inspection, I’ve realized that neither is fully true. The other five possible employee types do exist, and they’re worthy of study. 

The toxic categories (0 or 1 assets)

Passive employees are averse to discomfort, insubordinate, and indiscriminate in their uselessness. They aren’t very interesting, and they tend to be remarkably unsuccessful in any context. Related is the Passive-Aggressive, who is lazy and ornery, but strategic about how lazy to be. Passives almost never rise beyond the lowest levels, but the Passive-Aggressive’s destination is quite variable. In dysfunctional organizations, they can rise high. The Loose Cannon is insubordinate and not strategic, but dedicated. He will work hard toward something, but it may be detrimental. Ultimately, his complete lack of strategy means that his egotism and explosive nature are discovered early and he’ll rarely rise. Finally, the Yes-person is willingly subordinate, but neither strategic nor dedicated, the result of which is that he tends to support management verbally, but not follow through on account of incompetence. 

The normal categories (2 assets)

The Team-Player is the MacLeod Loser. She’s strategic and optimizes for minimal discomfort. Because of this, she aims for social approval. She’d rather be well-liked and “cool” than rise in the organization. She’ll manage her performance to the middle and do what it takes to get along with the team and her boss, but she won’t stay after 5:00. The Workhorse (MacLeod Clueless) is subordinate and sacrificial, but not strategic. She doesn’t recognize a good idea from a bad one and, therefore, indiscriminately works hard on the project put in front of her. Finally, the Self-Executive (MacLeod Sociopath) employee is strategic and dedicated, but not especially subordinate. Self-executive employees tend to view themselves as already in authority over their own careers. In subordinate roles, they see themselves as CEOs of one-person operations.

The conditional category (3 assets)

As I originally set this model forward, I assumed it to be contradictory to be subordinate, strategic, and dedicated. Someone who is strategic will either maximize personal benefit (dedicated, not subordinate) or minimize discomfort (subordinate, not dedicated). What I missed is that it can sometimes be strategic to be subordinate and dedicated– if there’s a career benefit in doing so. This is the elusive and rare eighth category, the Protege. This is the Self-Executive employee who has decided that the best thing for her career is to be taken under the wing of someone more experienced, and to sacrifice some autonomy in exchange for mentorship. It’s a trade. She gets executive buy-in to her career advancement and, in return, the superiors get work with a set of qualities (loyalty, dedication, and strategic insight) that would otherwise be paradoxical.

The Protege category is conditional because if the manager stops investing in her career, she becomes an ordinary Self-Executive. She’s conditionally subordinate, and will seek her own interests if the mentor abandons her. It’s also the most politically tricky, because it requires management to abandon neutrality. Taking one self-executive employee as protege can be seen (correctly) as “playing favorites” by the rest of the team. Workhorses (Clueless) won’t know they’re being disfavored and Team-players (Losers) won’t care enough to do anything about it, but the other Self-executive employees will be alienated.

The organizational destination of Proteges is unclear because it’s often an unstable arrangement. While they are typically fast-tracked to important roles, they are also vulnerable to the political standing of their mentors. Additionally, I should note that the Self-Executive vs. Protege classification is orthogonal to my split of the MacLeod Sociopath into the beneficial (Technocrat) and toxic (Psychopath) categories. Technocrats and Psychopaths are both capable of being strategically subordinate– or strategically insubordinate.

More on work cultures

Originally, I set forth the supposition that there are three types of work cultures:

• rank cultures, which value subordinacy.
• tough cultures, which value sacrifice.
• self-executive (originally market) cultures, which value strategy.

I’m going to make a couple changes to this model. The first is to note that tough and self-executive cultures share some similarities and both deserve the name of “market culture”, which I originally assigned only to the latter. The second is to add a fourth culture. That’s a guild culture, which is driven by the Protege’s conditional subordination. Guild and rank cultures are command cultures. We can again separate these four cultures based on two dimensions. The first dimension is whether the culture is centrally planned (command) or organic (market). The second is whether it is functioning or pathological.

The guild culture is a functioning command culture. There are masters and apprentices, and the relationship is one of mutual benefit. The one with more knowledge and experience is the mentor, and the less experienced inferior is the protege. This is the rarest of the four cultures, being associated with protectionism and pre-capitalistic intent, but the ideas behind it are still seen: most notably, in education. A guild culture’s purpose is to create value through the sharing of knowledge, and to capture it through loyalty in the well-taught. In 2013, with corporate loyalty seen as anachronistic, it’s a dying way of doing things. Companies are not likely to invest in employees when they live under the constant fear of them departing.

Rank culture, on the other hand, is a pathological command culture. Your manager is just your boss. He’s not expected to teach you anything or help you rise in the organization. He gives you orders and you follow them. Rank cultures are extortionate economies in which managers leverage their authority to unilaterally terminate an employee or, at the least, reduce her credibility to zero. In rank cultures, employees don’t work for the company, but for their immediate managers.

Self-executive culture is a functioning market culture. Employees are trusted with their own time and resources and form teams organically, and they’re responsible for delivering value to the business. In software, this is the open allocation methodology, which is sometimes mischaracterized as “work on whatever you want” when it is better described as “work directly for the firm”. This is a great arrangement for intermediate-level employees (who can direct their own progress) and experts, although it’s often not the best at mentoring beginners.

Finally, tough culture is a dysfunctional market culture. Like self-executive cultures, they emphasize individual accountability. However, they don’t trust the employee far enough to create a reasonable market for innovation. Employees must demonstrate value on a daily rather than yearly basis. Autonomy is reduced, deadlines are tighter, and performance and status assessments become so intrusive that they often cause underperformance.

Common transitions

Among these four types of work cultures, there seem to be four common transitions, two in which a functioning culture turns into its dysfunctional counterpart (guild into rank, self-executive into tough) and two in which a dysfunctional culture type evolves into the other (rank into tough, tough into rank). I’ll assess each of these, and what drives them.

Guild cultures turn into rank cultures when the organization either ceases to reward mentorship, or grows too fast to coach people along toward better capabilities. Managers are forced to balance the interests of their superiors against those of their subordinates, and are often required to side with those that sign their checks. If the organization doesn’t maintain a culture of mentorship, that goes away as psychopathic managers who “manage up” get promoted over those who favor their subordinates’ career interests. In the hyperfluid modern economy, most organizations are too paranoid about departing talent to make the long-term investment in their people that a guild culture requires. As the culture of the company’s management becomes increasingly psychopathic, the guild culture disappears and rank culture– serve your boss– is what’s left. Masters and mentors are replaced with rent-seeking position-holders.

Self-executive cultures devolve into tough cultures through a similar managerial devolution in which trust for lower level employees decays. Market cultures hold employees individually accountable for delivering something of value the organization, but the time interval (audit cycle) could be anything from minutes to years. What is the greatest amount of time with which the individual employee is implicitly trusted? Executives with itchy trigger-fingers tend to reduce that time interval and, as it goes to zero, what emerges is tough culture as deadlines become increasingly unreasonable.

Rank cultures are not stable because they tend to harbor underperformers. The best people leave, while those who commit mediocre work but keep their bosses happy are able to stay. Ultimately, this can only go so long before the top executives notice the problem and decide to intervene. Instead of firing being a rare thing that happens to the obviously toxic, some percentage of people will be fired “for performance” each year. Middle managers are not only unsafe, but targeted at higher rates than subordinate employees since they, for tolerating underperformance, are held responsible for the problem. The certainty and stability of the loyalist strategy disappear and people fight for visible work and to make their dedication and sacrifice visible. This turns the rank culture into a tough culture, a reinvention it must undergo because the long-term path of a rank culture is underperformance, lethargy, and death.

Tough cultures, similarly, are unstable. Normal people just can’t stand to work in them for longer than a few months, and very few companies will accept the constant turnover that tough culture induces. For the sake of personal and corporate stability, people start cutting deals, and the people who control the performance assessments become the new rank-holders, first informally, but with their status increasingly formalized over time as they win promotions through deal-making and extortion. One who can guarantee a positive review (which may not be the immediate manager) becomes one’s real boss. Thus, tough cultures return to rank cultures and, the tougher the culture is, the faster this occurs.

Are other transitions possible? Certainly they are, but I contend that they’re uncommon. Pathological work cultures rarely reinvent themselves as functional ones, so regeneracy seems rare. Moving from one pattern of dysfunction to another is easy and can be accomplished with top-down HR initiatives, but executives of large companies don’t really have the tools or incentives to bring a broken culture to fix itself. This seems to induce an “arrow of time” where the entropic direction is cultural failure.

We can model this as a Markov process. Let’s say that, each time step, 10% of self-executive cultures become tough cultures, 10% of guild cultures become rank cultures, 10% of rank cultures become tough cultures, and 40% of tough cultures become rank cultures. The healthy cultures have no in-flow, while there’s a shuffling back between tough and rank cultures. The long-term outcome is that an organization, left to its own devices, will spend four-fifths of its time as a rank culture, and one-fifth of its time as a tough (“crackdown”) culture. That seems about right. The process seems to be punctuated by upper management changes. The new bosses are chagrined by the inefficiency and underperformance they observe (or, perhaps, they were brought in because of underperformance). They kick the organization a few times and it becomes a tough culture. Toughness being unsustainable and deal-making surrounding credibility being inevitable, the best traders of credibility (or extortionists, for the black hat) congeal into the new definition of “rank”. Soon, they themselves become complacent and entitled… and the cycle repeats.

This is a follow-up to yesterday’s essay in which I confronted the MacLeod Hierarchy of the organization, which affixes unflattering labels to the three typical tiers (workers, managers, executives) of the corporate pyramid. Subordinate workers, MacLeod names Losers, not as a pejorative, but because life at the bottom is a losing proposition. Lifelong middle managers are the Clueless who lack the insight necessary to advance. Executives are the exploitative Sociopaths who win. I looked at this and discovered that each category possessed two of three corporate traits: strategy, dedication, and subordinacy (which I called “team player” in the original essay). I replaced team player with subordinacy because I realized that “team player” isn’t well-defined. Here, by subordinacy, I mean that a person is willing to accept subordinate roles, without expectation of personal benefit. People who lack it are not constitutionally insubordinate, but view their work as a contract between themselves and manager. They take direction from the manager and show loyalty, so long the manager advances their careers. Since they show no loyalty to a manager or team that doesn’t take an interest in their careers, they get the “not a team player” label.

MacLeod Losers are subordinate and strategic, but not very dedicated. They work efficiently and generally do a good job, but they’re usually out the door at 5:00, and they’re not likely to stand up to improve processes if that will bring social discomfort upon them. Clueless are subordinate and dedicated, but not strategic. They’ll take orders and work hard, but they rarely know what is worth working on and should not advance to upper management. MacLeod Sociopaths are strategic and dedicated, but not subordinate. The next question to ask is, “Is insubordinacy necessarily psychopathy?”, and I would say no. Hence, my decision to split the Sociopath tier between the “good Sociopaths” (Technocrats) and the bad ones, the true Psychopaths.

People who have one or zero of the three traits (subordinacy, dedication, strategy) are too maladaptive to fit into the corporate matrix at all and become Lumpenlosers. People with all three do not exist. A person who is strategic is not going to dedicate herself to subordination. She might subordinate, in the context of a mutually beneficial mentor/protege role, but general subordination is out of the question. Strategic people either decide to minimize discomfort, which means being well-liked team players in the middle of the performance curve– not dedicated over-performers– or to maximize yield, which makes subordinacy unattractive.

What I realized is that, from these three traits, one can understand three common workplace cultures.

Rank Culture

The most common one is rank culture, which values subordinacy. Even mild insubordination can lead to termination, and for a worker to be described as “out for herself” is the kiss of death. Rank cultures make a home for the MacLeod Losers and Clueless, but MacLeod Sociopaths don’t fare well. They have to keep moving, preferably upward.

While the MacLeod Clueless lack the strategic vision to decide what to work on, their high degree of dedication and subordinacy makes them a major tactical asset for the Sociopath. The Clueless middle manager becomes a role model for the Losers. He played by the rules and worked hard, and moved into a position of (slightly) higher pay and respect. 

Rank cultures have, within them, a thermocline. From worker to middle manager, jobs get harder and require more effort to maintain and achieve. Below the thermocline, one really does have to exceed expectations to qualify for the next level up. Above the thermocline, in Sociopath territory, the power associated to rank starts paying dividends and jobs get easier as one ascends, rising into executive ranks where one controls the performance assessment and can either work only on “the fun stuff”, or choose not to work at all. Rank cultures require this thermocline, an opaque veil, to keep the workers motivated and invested in their belief that work will make them free. That is why, in such cultures, the strategically inept Clueless are so damn important.

Tough Culture

Rank culture’s downfall is that, over time, it reduces the quality of employees. The best struggle to rise in an unfair, politicized environment where subordination to local gatekeepers (managers) is more important than merit, and eventually quit or get themselves fired. The worst find a home in the bottom of the Loser tier, the Lumpenlosers. At some point, companies decide that the most important thing to do is clear out the underperformers. Thus is born tough culture. Rank culture values subordinacy above all else; tough culture demands dedication. Sixty hours per week becomes the new 40. Performance reviews now come with “teeth”.

Enron’s executives were proud of their “tough” culture, with high-stakes performance reviews and about 5% of employees fired for performance each year. The firm was berated for its “mean-spirited” and politicized review system that, in reality, is no different from what exists now in many technology companies. This is the “up-or-out” model where if you don’t appear to be “hungry”, you’ll be gone in a year or two. Those who appear to be coasting have targets on their heads.

Over time, tough culture begets a new rank culture, because the effort it demands becomes unsustainable, and because those who control the new and more serious performance review system begin using it to run extortions based on loyalty and tribute rather than objective effort. They become the new rank-holders.

Market Culture

Rank culture demands subordinacy, and tough culture demands dedication. Market culture is one that demands strategy, even of entry-level employees. You don’t have to work 60-hour weeks, nor do you have to be a well-liked, smiling order-follower. You have to work on things that matter.

Rank and tough cultures focus on “performance”, which is an assessment of how well one does as an individual. If you work hard to serve a bad boss, or on an ill-conceived project, you made no mistake. You were following orders. You had no impact, but it wasn’t your fault, and you “performed” well. Market cultures ignore the “performance” moralism and go straight to impact. What did you do, and how did it serve the organization? Low-impact doesn’t mean you’ll be fired, but you are expected to understand why it happened and to take responsibility for moving to higher impact pursuits.

People who serially have low impact, if the company can’t mentor them until they are self-executive, will need to be fired because, if they’re not, they’ll become the next generation’s subordinates and generate a rank culture. Firing them is the hard part, because most of the people who conceive market cultures are well-intended Technocrats (or, in the MacLeod triarchy, “good Sociopaths”) who want to liberate peoples’ creative energies. They don’t like giving up on people. But any market culture is going to have to deal with people who are not self-executive enough to thrive, and if it doesn’t have the runway to mentor them, it has to let them go.

A true market culture is “bossless”. You don’t work for a manager, but for the company. You might find mentors who will guide you toward more important, high-impact pursuits, but that’s your job. In technology, this is the open allocation methodology.

Why Market Culture is best

Market culture seems, of the three, the most explicitly Sociopathic (in the MacLeod sense). Rank cultures are about who you are, and how well you play the role that befits your rank. Tough cultures are about how much you sacrifice, and democratic in that sense. Market cultures are about what you do. Your rank and social status and “personality” don’t matter. Is that dehumanizing? In my opinion, no. It might look that way, but I see it from a different angle. In a rank culture, you’re expected to submit (or subordinate) yourself. In a tough culture, your contribution is sacrifice. In a market culture, you submit work. Of these three, I prefer the last. I would rather submit work to an “impersonal” market than a rank-seeking extortionist trying to rise in a dysfunctional rank culture. 

What I haven’t yet addressed is the cleavage I’ve drawn within the MacLeod Sociopath category between Technocrats and Psychopaths. The most important thing for an organization is the differential fitness of these two categories. Technocrat executives are, on average, beneficial. Psychopaths are unethical and usually undesirable.

Pure rank cultures do not seem to confer an advantage to either category. Tough cultures, on the other hand, benefit Psychopaths who find an outlet for their socially competitive energies. Ultimately, as the tough culture devolves into an emergent rank culture, Psychopaths thrive amid the ambiguity and political turmoil. Tough cultures unintentionally attract Psychopaths.

What about market cultures? I think that Psychopaths actually have a short term advantage in them, and that might seem damning of the market culture. This is probably why rank cultures are superficially more attractive to the Clueless middle-managers, with their dislike of “job hopping” and overt ambition. On the other hand, and much more importantly, market cultures confer the long-term advantage on Technocrats. They’re “eventually consistent”. To thrive in one for the long game, one must develop a skill base and deliver real value. That’s a Technocrat’s game.

The MacLeod Model of organizational sociology posits that workplaces tend toward a state in which there are three levels:

• Losers, who recognize that low-level employment is a losing deal, and therefore commit the minimum effort not to get fired.
• Clueless, who work as hard as they can but fail to understand the organization’s true nature and needs, and are destined for middle management.
• Sociopaths, who capture the surplus value generated by the Losers and Clueless. Destined for upper management.

Venkatesh Rao has a brilliant analysis of these three tiers as they play out in the sit-com, The Office. 

I’m going to propose the existence of a fourth subset: the Technocrat. Before doing that, it’s important to assess the forces that generate these tiers, and why I think the MacLeod classification isn’t adequate.

Effort and strategy

Losers are not “losers” in the sense of being unpopular or contemptible people. Here, “Loser” means “one who loses”. In fact, they’re often well-liked and good people. However, they’re aware that employment is a better deal for the other side than it is for them. What they want most is to be comfortable. They don’t want job insecurity or too much change. They’re not “losing”, so much as they’re selling risk, in their poorly-paid jobs. They prefer contests where the points don’t matter (e.g. the Party Planning Committee in The Office) and the comfort of a stable group that will protect them. At work, they generally aim for the Socially Accepted Middling Effort (SAME). They’re not lazy, but the largest influence on how hard they work is social approval. They don’t want to be perceived as slackers, nor as overachievers, so they manage their performance to the middle.

Clueless are the hardest workers. They work as hard as they can, out of a sense of loyalty and ethical obligation. There’s an adverse selection at play that favors the untalented, because people who are naturally talented and hard workers tend to threaten Sociopathic colleagues and will be sabotaged. The survivors tend to be the less capable. Michael Scott, again borrowing from The Office, is a clear example of this. While he’s incompetent, he clearly puts everything he has into his work, having no social life outside of it. If he were more intelligent, he’d either have been tapped for a better role, or he’d be perceived as a threat and be sabotaged by an ambitious Sociopath. However, the less effective and capable Clueless are clearly destined for terminal middle-management roles that Sociopaths don’t want, so this adversity doesn’t often befall them. 

Sociopaths are strategic in their work ethic, but also flexible. As Venkat describes, they’ll fall to the outright bottom, effort-wise, if that frees up resources to impress someone who matters. They have no qualms about reducing their effort to zero in an environment where social attractiveness is more important. However, they’ll also contribute immense bursts of energy when a promotion is available. One core Sociopath skill is assessing whether it’s advantageous to work hard and, when not, to slack off and focus on social polish.

Common traits of the tiers

Of these three subsets, each pair of them has a unifying trait that is considered an asset by the corporate world. Losers and Sociopaths are strategic, Clueless and Sociopaths are dedicated, and Losers and Clueless are team-players. Each of these deserves assessment.

Team-playing (Losers and Clueless)

Companies prefer employees who will prioritize social approval from the team over personal ambitions or needs, and call such a person a team player. The alternative is the out-for-herself careerist who expects interesting work and upward mobility. The selling trait of team players is that they don’t have to be explicitly motivated “from above”. Wanting to do good by the people around them will motivate them organically “for free”, and they’ll ignore being underpaid, ignored, and given few opportunities to advance if the group’s approval is enough to indulge their esteem needs.

Losers are team-players because they want social approval. They want the comfort of being in rather than vying for up. They’re happy with the trophy of ascent into a meaningless in-crowd (in The Office, the Finer Things Club). Their goal is to be cool. Clueless, however, want to be “in charge”. What turns them into team players is the fact that they can be motivated with meaningless leadership accolades, or even undesirable tasks dressed up as positions of power (in The Office, Dwight). Clueless, in general, can’t recognize the difference between the genuine power sought by Sociopaths, social approval sought by Losers, and the ceremonial non-power that Sociopaths and other Clueless generate to keep them motivated.

Of the three traits I will analyze (team-playing, dedication, and being strategic) the most important one for a subordinate position is team-playing. Even if a person is highly competent, if she’s not well-liked by her team, she won’t be effective in a low-level position, because no one will help her. Subordinate positions never involve enough autonomy for a person to have a real achievement on her own. As Venkat Rao correctly assesses it, Sociopaths in subordinate roles have a short lifespan, limited by their willingness to run a team-player charade. It’s up-or-out for them. Ryan, in The Office, does this brilliantly. He uses his relationship with air-headed Loser Kelly to hide his true nature and underplay his threatening intelligence– seeming like an incompetent Loser– but once he finds common ground (his MBA degree) with CFO David Wallace, he takes the chance to jump and, on success, dumps her immediately.

Dedication (Clueless and Sociopaths)

For Losers, most of life is outside of work. Losers will put in their 40 hours, but if you ask one to work a weekend or do undesirable tasks that are way outside of her job description, you’ll get resistance. For the Loser, it’s “just a job”, and not something that has the right to dominate a person’s entire life. Losers aren’t lazy or apathetic, but they’re rationally disengaged. A loser recognizes that she can get an equivalent job at another company, so it’s group cohesion only that keeps them in place.

Clueless and Sociopaths, on the other hand, can work 90 hours per week without complaint. They’ll do their best to meet unreasonable requests from above, but their motivations are very different. Clueless are driven by a misguided sense of corporate loyalty, both above and below them. The Clueless middle-manager (or over-performing team member) is willing to please her boss, on whom she depends for her connection to the company (to which she feels a debt of gratitude). She’s also willing to pick up the slack of the Losers on her team, out of a sense of personal and possibly parental loyalty to them.

Sociopaths are dedicated for a different reason. Like anyone else, a Sociopath would prefer not to work long hours or do unpleasant tasks, but their pain tolerance is extremely high, because the corporate game is fun to them. For a Sociopath, a 90-hour work week is like spending that much time playing a video game. It’s not how most adults would choose to spend their lives, but it’s not taxing, boring or painful either. If the rewards are there, the Sociopath will drop everything and put in the hours.

For a middle manager, dedication is the most important trait. Middle managers frequently find themselves in two jobs that are often at odds. On one hand, they have to clean up the messes left by rationally disengaged Loser subordinates. On the other hand, they must please the hard-driving Sociopaths above them. This generates not only a lot of work, but an incoherent, heterogeneous mess of it. Frequently, they end up working on “whatever’s left” and putting in a lot more energy than the tiers below and above them. The Loser subordinates don’t work as hard as they do. The Sociopath executives have enough power to control the division of labor and definition of “performance”, so they don’t have to work hard. Middle-managers get stuck in the middle, and it takes dedication to survive it.

Strategy (Losers and Sociopaths)

Losers and Sociopaths might seem to be polar opposites, but they also share an important trait: they’re strategic. They’re realistic in their assessment of what efforts will be fruitful and, unlike the Clueless with their unconditional work ethic, they allocate their time and energies only toward work that seems to be worth a damn. In this, they tend also to be able to relate amicably, because their strategies rarely conflict.  They want different things. Losers want to minimize discomfort and to be “cool” as defined by the in-crowd where they are. Sociopaths want to maximize personal reward and rise into the in-crowd that actually has power.

Strategic workers tend not to waste time. Losers work efficiently but tend to do as little as they need to retain social acceptability. Contrary to stereotype, they don’t do “the minimum not to get fired”. They modulate their efforts to the middle, not wanting a slacker reputation, but not wanting a “busy bee” reputation that will overload them with undesirable work. Sociopaths (and Technocrats, to be discussed later) work on the stuff that benefits their careers, and ignore whatever doesn’t.

For upper-management roles, being strategic is the most important trait. A non-strategic manager or executive will put a lot of effort into pursuits of low or even negative value. That can be acceptable for a middle manager. The Sociopaths above will set priorities, and direct him, while the social-approval mechanisms of the strategically-aware Losers will keep the team from going completely off the rails. Teams can protect themselves, in the short term, from off-the-rails Clueless management. A non-strategic executive is dangerous, if not untenable. Losers, in fact, tend to be better picks for executive roles than Clueless. This explains why, after Peter outs himself as a disengaged Loser to “The Bobs” in Office Space– while office conformity demands that subordinates fake Clueless earnestness around authority– they describe him as “a straight shooter with upper management written all over him”. He’s strategic. He understands that his current job is not worth doing.

Other possibilities…

All three of these traits are attributes that corporations view as assets: being a team-player, dedication, and being strategic. I’ve painted a picture in which each of the three MacLeod tiers has exactly two of the three. Losers are strategic team players, but not dedicated. Clueless are dedicated team-players, but not strategic. Sociopaths are dedicated and strategic, but not team players. This brings us to the question: why should an employee have exactly two of these seemingly orthogonal capabilities? What happens to people with zero, one, or three?

Deficient categories (0/3 and 1/3 traits)

If someone’s neither dedicated nor strategic, it doesn’t matter much whether that person’s a team player or not. A team player sacrifices personal ambitions for the health of the team, but people who are neither dedicated nor strategic have nothing credible to sacrifice. These fall into the bottom of the Loser category: Lumpenlosers.

Dedicated, non-strategic, non-team-players are Loose Cannons (see: Andy in The Office). They’re driven by ego, but have no insight into whether what they’re doing serves any purpose (personal or organizational) at all. They tend to eagerly throw themselves into battles with no idea where they will lead. Either they are fired, or they become Lumpenlosers as well, being tolerated for the amusement they provide.

Finally, to be strategic but neither a team-player nor dedicated is almost a contradiction in terms. A strategic person will recognize that one or the other is necessary in order to retain employment in the long term. So, the only time this constellation occurs is when a person has little interest in staying with a company. They usually quit or get fired.

Unicorns? (3/3 traits)

Are there people out there who are strategic, dedicated, and team players? I would also argue that this arrangement is contradictory, at least in a subordinate role. A strategic person will either aim for minimal discomfort and pain, or for maximal benefit. The first category will avoid conflict and disharmony (team player) but not work long hours, especially not to an extent that hurts the group (by making others look bad in comparison). On the other hand, the yield-maximizer will work very hard (dedication) but not for the benefit of a social group coalesced around someone else’s purpose. People who are strategic and dedicated will demand important roles and interesting work, which means they’re not likely to be perceived as team players.

This is not to say, however, that it’s impossible or even rare for a person to be strategic, dedicated, and a good person. What I do mean to imply is that strategic and dedicated people don’t accept subordination. Although they will work for altruistic purposes or the good of “the team”, they do it on their terms. In fact, I would argue that among the most important players in the modern economy, a fair number of them fit this exact description. Like MacLeod Sociopaths, they’re dedicated and strategic. However, the term “Sociopath” doesn’t apply, because they aren’t bad people, and they’re not willing to rise by being unethical. They want to win, but fairly. This requires revisiting the Sociopath category.

Are MacLeod Sociopaths really sociopaths?

I would argue that the Sociopath category should be split into two subsets: Technocrats, and the true Psychopaths.

It’s important to address the term sociopath. It’s no longer used in psychiatry, having been replaced by psychopath. A psychopath is a person without a conscience, and that’s about as close as modern psychiatry gets to calling someone “a bad person”. Most psychopaths are, as typically defined, bad people. Their lack of empathy and concern for others leads then toward reckless and harmful behavior. Whether this is mental illness or sane moral depravity is almost a religious question, but either way, psychopaths aren’t desirable in an organization, but many are very successful climbers of institutional ladders. The lower classes of psychopaths end up as common criminals, but the smartest and most socially adept psychopaths develop strategies for externalizing costs and taking credit for others’ accomplishments. They are disproportionately common in the upper ranks of corporations.

Sociopath is a pop-psychology synonym for “psychopath”, most likely persisting because the popular ear conflates the latter with “psycho” or “psychotic”, which psychopaths are clearly not. It is not even clear that psychopaths are mentally ill. I would argue that, in a prehistoric evolutionary context, their lack of emotional attachment to others made them individually successful (high rates of reproduction, at least for men) at the expense of group harmony and stability. In modern society, they are the cancer cells– individually fit at the expense of the large, complex body of civilization. This is different from typical mental illness (especially psychosis) which is undisputedly pathological, making the individual less fit.

Psychopaths are egotistical and usually unethical. Above all, they desire social status. Money and power are only interesting to them so far as they confer an elevated position over others. This characterization, one hopes, does not apply to everyone who is strategic and dedicated within an organization. I find it clear that it does not. There are good people who are strategic and dedicated. So I add a fourth category: the Technocrat. So I discard MacLeod’s Sociopath category, and split it into the Technocrat and the true Psychopath.

In this usage, Technocrat pertains more to the abstract principle of technology– the use of knowledge in pursuit of mutual benefit– than to any concrete device. Technocrats are dedicated and strategic and, like Psychopaths, they want to win. What differentiates them is that they don’t want to make others lose. Technocrats have a positive-sum mentality and a desire to make improvements that benefit everyone. True psychopaths despise what they perceive as human weakness and want to dominate people. Technocrats are competing against “the world” in the effort to make it better than it has ever been.

Because Technocrats like to improve things, they extend this mentality to their work and themselves. They want to be more skilled, and more autonomous, so they can achieve more. They’re dedicated, because it requires work to find “win-win” opportunities. They’re strategic, because what they do tends to require creativity. In general, they’re not team players. Losers are team players because they fear social disapproval, and Clueless if they perceive their role as leadership (even if it’s objectively not). Psychopaths view the team as something to exploit (for personal gain) and to dominate (for enjoyment). Technocrats want to improve the team, often in spite of itself. This makes them good leaders, but they turn out to be shitty subordinates. That, in fact, is the Technocrat’s downfall. Of the four classes, they are the absolute worst in subordinate positions. Psychopaths hate subordination as well, but they’re better at failing silently for long enough to move up.

The MacLeod model correlates psychological traits with organizational position, and the Technocrat is difficult to pin down. Other categories are much easier. Losers cannot typically rise into management because they aren’t dedicated. Clueless should not become executives because they aren’t strategic. (It happens, but they usually get fired at some point.) Psychopaths can rise without limit, but their lack of a team-player ethos means they’re fired if they can’t find a route. There isn’t a clear position in the traditional managerial hierarchy for the Technocrat. Organizations would probably prefer to have Technocrats over Psychopaths in upper management, if they were rational entities. They’re not, and for a variety of reasons, when Technocrats and Psychopaths battle, the Psychopaths usually win.

Technocrats don’t have a well-defined home in the white-collar corporation. They despise the pointless busywork of subordinate positions, so they don’t do well in the Loser circuit. They tend to be logical truth-seekers, so the Clueless world of middle-management is too full of self-deception for them. Finally, amid the zero-sum in-fighting of Psychopaths in the executive suite, they often lose. Why do they often lose? That I will address below.

Some Technocrats have found a way to become highly-paid individual contributors, such as in academia, research, and software engineering. Unfortunately, this isn’t a stable arrangement for most. Academia has taken a Clueless direction of late: graduate students and pre-tenured professors are grunts, and tenured professors are (semi-autonomous) middle managers chasing rainbows. I consider most of them non-strategic because they lack interest in the practicality of their work, a behavioral pattern that has reduced their social status over time. Software engineering, on the other hand, is mostly a (better-paid) Loser’s world, because most of the work that professional developers get is line-of-business dreck that isn’t intellectually challenging, and not worth the dedication that a genuinely important or interesting project would deserve.

The typical career of a Technocrat looks similar to one of a Psychopath: job hopping, up-or-out gambits, and the obvious prioritization of a personal strategy over “team player” social acceptability. The difference is the purpose toward which she aims. The Technocrat wants to become really great at something and do something good for the world. The Psychopath wants to climb old-style, increasingly anachronistic, industrial hierarchies and dominate (or, at least, exploit) others. Both are after power, but they define it differently. Technocrats seek the power to help people; Psychopaths want power over people.

One might suspect that Technocrats should succeed as entrepreneurs, and this is probably the Technocrat’s best bet. Rather than attempting to find a decent role in an existing, dysfunctional organization that it will be impossible for her to fix, she should create a new one. Then, she has no conflict between her strategic and dedicated nature and being a “team player”, because she has built and defined the team.

What I would say, however, is that the venture-capital-funded startup ecosystem (VC-istan) is not a Technocrat’s paradise, despite its pretensions to that effect. The actual ethical behavior of the leadership at most of these VC darling startups is old-style managerial Psychopathy. Why is it this way? To answer that, one needs to understand what VC-istan actually is: one of the first postmodern corporations. VCs are supposed to be in competition with one another, but they collude. They decide, as a group, who’s hot and who’s not, and what valuations will look like in each season, and they get together and co-fund startups. There is no market economy. Rather, funding decisions are made by a command economy driven by social consensus among an in-crowd (partners at influential VC firms) and those who wish to join them.

One might think that VC-funded startup founders are Technocrats. Not likely. These so-called CEOs are actually mid-level Product Managers within the postmodern corporation of VC-istan. Some are ascendant Psychopaths seeking a transition to a more senior (“entrepreneur-in-residence”, VC associate, corporate executive) role and others are Clueless “true believers” who fail to recognize that, due to their investors’ unilateral control not only over their current projects but over their long-term reputations, they’re nothing but eager middle managers.

So where are the Technocrats, then? Over time, they tend to fail out of hierarchical organizations, being ill-equipped to fight against the Psychopaths who tend to defeat them. As VC-istan increasingly devolves into a postmodern corporation (rather than a real market, with– imagine this!– actual competition among investors) they will be increasingly out-of-home there, as well. I don’t know where they’ll go. My guess is that the rising generation of Technocrats will find a way to democratize business formation, with crowdfunding (e.g. Kickstarter) being an obvious first step in that direction, and presumably a lot more to come.

Why Psychopaths beat Technocrats

Why do the zero-sum, destructive Psychopaths defeat the positive-sum, creative Technocrats? To answer this, it’s important to understand credibility, which is an umbrella term for intangible assets that institutions create in order to rank people by perceived merit.

How do organizations decide how to compensate people, and whom to promote? When a person starts a new job, her salary is based on economic conditions and her negotiation skill much more than any objective definition of merit. Companies, begrudgingly, accept this. They recognize the tradeoff between operational efficiency and fairness in compensation, and will gladly adapt salaries to conditions. However, companies prefer to believe that they get the division of labor and recognition right. It’s important for them to maintain this fiction, because it allows them to believe that, although they know their compensation schedule to be unfair, they know exactly how unfair it is and can reduce the injustice (not out of ethical principle, but because it’s a morale risk) over time. If Bob and Mark are both Level IV software engineers making $100,000 and $120,000 per year, respectively, Bob can receive better annual raises until they’re at parity.

This is what professional ladders and job titles are for. The firm wants to believe (or, at least, wants the Clueless to believe, that often being enough) that, while small injustices are tolerated in specific individual compensation, that salary ranges shall be set according to job descriptions, which will be assigned according to pure merit. Someone who is “platonically” at Level IV might get a higher salary based on prior compensation, negotiation skill, and market conditions, but he should never get a Level-V title… until he earns it. Titles, as the organization perceives them, must correspond to personal merit and work performance, not external conditions.

This is credibility, which represents the company’s degree of trust in an individual. Compensation is what a person takes out of a company. Credibility is what the firm thinks the person puts into it. Job titles are a powerful form of credibility, being transferrable to some degree across companies. So-called “performance” reviews exist to calibrate private credibility based on a person’s work history, and may eventually result in public credibility changes through promotions (or demotions and terminations). Societies understand that resources (power, money, information) sometimes accrue to unworthy or even dangerous individuals, and that there is nothing to prevent “the bad rich” from acquiring mere commodities once this has happened, but the sacred intangible of trust is supposed to be above that. Credibility is the corporate analogue of trust, invented because interpersonal trust becomes sparse at scale. Large organizations recognize that genuine trust, built through direct interaction, is not enough to tie people together, so they need to invent a legible pseudo-trust in order for anything to get done. Credibility is a currency that corporations mint in order to make statements about how far a person can be trusted. You’re not supposed to be able to get credibility through trade. It should be a reward for the demonstration merit only.

Credibility isn’t just a vague, academic notion. It has actual effects. For example, a common way for a company to do a layoff is to select levels at which it is overstaffed, and terminate the highest-compensated at that level. The idea is that employees at each level are equal in productive value. It’s corporate consistency. Thus, the most marginal employees, who should be let go first, are the highest-paid at the targeted level. Let’s say that the Level IV salary range is $80,000 to $120,000 and the Level V range is $100,000 to $160,000. It’s dangerous to be a Level IV at $120,000– but very safe to be a Level V at the exact same salary.

Is this regime exploitable? Of course. Clueless might believe that there’s such a thing as a “platonic” Level IV, and that people will be accurate assessed and promoted to their level of ability. That’s not true. There is no “platonic” Level IV or Level V. There will be guidelines based on work experience and interview performance, and then myriad possible exceptions. A wise negotiator slotted for Level IV, if he knew the company’s HR infrastructure, would target his salary history and expectations toward $125,000, making him ineligible for a Level-IV position. Would the hiring manager say, “We can’t meet that”, and turn him away? Or would she bump him to Level V, not only justifying his salary, but improving his job security, leadership opportunities, and level of respect within the company? Unless he were very clearly ineligible for a Level-V position, the latter would happen. So he would, in effect, be using his negotiation skills to win credibility. In the real world, credibility is just as negotiable and tradable as “harder” currencies like money, power, and information. It’s not “supposed” to be that way, but it is.

Losers care about credibility, but only enough to retain employment. Once they have enough of it, they focus on side games in which those games’ local definitions of credibility and status don’t really matter, in that they have no effect on personnel decisions or compensation. Clueless believe deeply in credibility and go about earning it “the old-fashioned way”, which is to earn it through hard work. Psychopaths, on the other hand, are the quickest to actually realize what credibility is: a corporate fiction. In reality, it’s a commodity like any other. If they need someone to vouch for them, they find a way to buy it. Psychopaths bribe and extort their way into credibility. They take credit for others’ work, they lie, and they find ways to trade social assets (including titles and “job performance”) that aren’t “supposed” to be for sale.

How do Technocrats handle credibility? I’m not sure. Since the intended effect of corporate credibility is to create a global social status in large groups that would otherwise not have a clear rank ordering, thus generating a sort of “permanent record” that’s ripe for abuse by power, it seems naturally opposed to the Technocrat ethos. However, it’s also clear that corporations need to invent credibility, because interpersonal trust is too sparse at scale for large organizations to function, and credibility becomes a lubricant. To the extent that Technocrats accept credibility’s existence, they tend to treat it as an engineering problem. I think the Technocrat’s objective is to fix credibility: to redefine it so that it can’t be traded, bought, or won through extortion, and to make it an actual dimension of merit. Of course, this is a hard, if not impossible, problem. Psychopaths take a much easier route with more personal benefit: they find ways to exploit it.

Indeed, these four categories can be framed in terms of psychological reactions to the divergence between true merit and corporate credibility:

• Clueless deny it and persist in the just world fallacy. Indeed, credibility’s root power is in its ability to motivate and impress the Clueless. 
• Losers accept the crookedness of the corporate game and disengage, grabbing just enough credibility to avoid adversity.
• Psychopaths become crooked themselves, which is the fastest path to personal benefit, and ultimately win not only credibility for themselves but the capacity to modulate others’ credibility, which is corporate power.
• Technocrats attempt to fix the game, often altruistically through openness, transparency, and anti-hierarchical corporate structures. So far, they haven’t shown much success in deploying their vision at scale.

Between Psychopaths and Technocrats, who is more likely to climb the corporate ladder? Unfortunately, the advantage is with the former. Technocrats have to change people, while Psychopaths exploit them as they are.

Corporations, being pre-industrial in their ideology, have relied heavily on credibility and personal relationships for an obvious reason. There weren’t many hard problems for these institutions (rent-seekers that used technological innovation, but rarely created it) to solve, and there was no other way to evaluate people. Once the hard intellectual challenges have been overcome and it’s a risk-averse, stable organization, then how does it define the “best” who deserve leadership positions? How does one define “merit”? The Losers don’t attend that debate, because they don’t care. The Clueless say, “Hard work”. Technocrats argue for creativity and insight, still wanting to tackle hard problems that the now-stable and risk-averse organization believes it has outgrown. Psychopaths form an alliance with the Clueless, recognizing them as effective (in well-defined roles) but non-threatening. What’s built up, then, is a concept of “performance” that, to the Clueless, looks like a commodity earned only through hard work: a credibility. Clueless provide the muscle and blind support that enable credibility to be manufactured; Psychopaths define it. However, the Psychopaths are always careful to define performance with enough back-doors that they can win, regardless of whether they wish to work hard. At the top, this is especially easy. If you control the division of labor, you get to write your own performance review.

What Psychopaths recognize is that credibility can always be bought on a black market. There are always ways to get it, and often the illicit ones are more effective than the straightforward path. Technocrats understand this as well, but they often find it morally objectionable to start trading. It feels like cheating to them, and the worst varieties of credibility-trading (which generally amount to professional extortion) they refuse to use at all.

Can Technocrats win?

Psychopaths and Technocrats are destined for conflict. Psychopaths invent social credibilities to win the support of the Clueless and put themselves at the top of organizations. Technocrats see a crooked game and try to fix it, often with radical honesty. If the Technocrats succeed, they’ll undermine the work of the Psychopaths. This becomes a fight to the death. The character of an organization will be determined by which of these two categories wins. Ultimately, most organizations will be run by Psychopaths who superficially adopt the appearance of Technocrats. This becomes increasingly the case as corporations become risk-averse and self-protective. The positive-sum “win-win” outcomes that Technocrats seek exist, and they’re all over the place, but they never come without risk. Once the company decides that creative risks are intolerable, what’s left is zero-sum social-status-driven squabbling.

The MacLeod hierarchy applies best to the modern white-collar corporation, whose modern incarnation was developed in the 1920s. At the time, there were a decent number of Technocratic leaders, but over time, corruption set in. By the mid-1970s, it was clear that Psychopaths were going to take over, and the “greed is good” 1980s saw that through. Basic research was cut, academia turned into a pyramid scheme, and well-positioned corporate executives made millions. Psychopaths gutted and looted corporations, leaving husks– large, powerful institutions whose beneficial purposes had been discarded, leaving mere patterns of externalized costs and value-capture by the Psychopaths. Where’d the excluded Technocrats go? Well, all over the place, but the most well-known cohort moved to Silicon Valley– before it was cool.

Silicon Valley is not a Technocrat haven any more. If nothing else, one need only look at house prices in the Bay Area. In cases of extreme geographic scarcity (e.g. San Francisco, Manhattan) house prices might be explicable by supply and demand in a fair, because supply responds slowly to economic circumstances while the demand curve moves quickly. However, when extreme housing prices persist over the long term, and over a large and mostly suburban area where there is no natural geographic scarcity, this suggests market manipulation and NIMBYism. That’s the surest sign ever that Psychopaths are winning. I am not saying this to rag on California. (I live in Manhattan; we have expensive real estate and Psychopaths, too.) In fact, had California’s real estate problem reversed itself, I’d argue that it was a transient market phenomenon and not Psychopathic victory. However, even when the economy softened, Bay Area real estate remained pricey. That’s a primary indicator that the Psychopaths have started to win. Psychopaths love when real estate is expensive, because they can use physical position to display dominance. Technocrats, on the other hand, love New Places, because New Places are positive-sum– you can build cool things on inexpensive, unused territory and improve it. The Technocrats poured into California when it was a geographic New Place and land was cheap. Now the New Places are elsewhere. It’s not clear what the next Technocratic New Place is, or even if “Place” still needs to be a geographic location, but it’s no longer Northern California.

If I had to guess, though, I’d bet that within the next 10 years, VC-istan will fall under the weight of its own organizational Psychopathy. I don’t have enough personal experience to opine on whether VCs themselves are Psychopathic, but the VC darlings thatI’ve known well have been run by some horrible people. Mark Pincus has been most overt about his psychopathy, but his behavior is far from atypical among the sorts of people who win in this bubble-world. Once, I had to leave a junior-executive position (for which I had left Google) at a brand-name, VC-funded startup at 3.5 months because I refused to sign an affidavit that not only contained perjury, but probably would have Pincus’d ten on my colleagues who had joined early and had “too much” equity. The Psychopathic management of that company spent months afterward attempting to destroy my reputation. How I overcame that adversity deserves its own essay, for another time…

Psychopaths defeat Technocrats in an organization where the work is intellectually easy, creatively non-demanding, and social status ends up trumping ability. That describes most organizations, because most companies are too risk-averse to do anything hard or important. Needless to say, Psychopaths love economic bubbles– exploitable, chaotic optimism without substance– and the 2010-13 “social media” affair clearly qualifies. However, this bubble’s very different from the last one. In the 1997-2000 bubble, startups were overvalued by the market. Wall Street provided the fools. In this one, market valuations appear reasonable. Investors aren’t going to fall for that one again. This bubble is in the unduly high value assessed, by young talent, to subordinate positions in these startups. (I wrote this, last summer, to contribute to its inevitable “pop”.) The fools aren’t coming form Wall Street, but fresh out of school. Most employees of these VC-funded “tech startups” believe they’re 6 months away from investor contact, real job titles, and the chance to be a founder in the next startup. They’re wrong. Long before they can collect the career assets they’ve been promised, this bubble will have popped and washed back to sea, leaving them with useless work experience and, thanks to the high cost-of-living in the startup hubs, no savings. The 1990s dot-com bubble wrecked a few careers and spilled a lot of rich peoples’ money. The 2010s bubble will spill a little bit of rich peoples’ money and wreck a lot of careers– mostly, those of young technologists trying to establish themselves. I would argue that this makes it worse.

What I hope to see during 2013, and the coming years, is a Flight to Substance. I want the best people– investors, entrepreneurs, engineers– to realize that they’ve been hoodwinked by VC-istan’s shallow reinvention of the corporate system as something different and “cooler”, and to demand a return to Real Technology. I want to see better ideas, better companies, and better cultures. I want to see funding for research and development, so that people can do intellectually interesting work without being thrown into the secondary labor market that academia has become. I want to see a world in which people actually care about solving hard problems and delivering real value. When this happens, the Technocrats can win again.

Any creative field undergoes periods of divergence and convergence, and technology is no exception. Right now, we’re in the late swing of a divergent phase, with a plethora of new languages, frameworks, paradigms and methodologies so vast that it’s impossible, at this point, even to know a respectable fraction of them. There are “back-end programmers” who know nothing of Javascript, and “front-end guys” who’ve never used a profiler. That will end, as people grow tired of having to learn a new technology stack with every job change, and also as the dimensionality of the bilateral matching problem between engineers and employers becomes intolerable. As painful as convergence can be, such a time will come out of necessity.

For a single company, convergence is often enforced internally, with “approved tools” lists and style guides. Often the communication that drives these decisions takes a familiar form: flame wars.

These partisan fights are common in technology. There’s one set of programmers who believe Java is the only language that has a right to exist and that, if you’re not using an IDE, you’re using “stone tools”. There’s another contingent that thinks everything should be written in Ruby, because that’s what Rails is in and why do we need another goddamn language? There’s a third that’s fixated on C++ on the basis that, if you can’t manage memory, how can you make sure an application performs? For now, I don’t care who’s right in this– really, that depends on the problem, because there clearly isn’t “one language to rule them all”– and language or style comparisons are not what I care to discuss today. I think we can all agree these flame wars are stupid and counterproductive. Do tabs/spaces debates really require long email chains? No, they don’t.

This, if anything, is the thing I dislike second-most about programmers. The worst thing about programmers is that most of them (although this is a largely a product of a corporate environment that rewards mediocrity) lack taste and curiosity, and therefore never become competent. The second-worst is that, among those who have taste, most of the heated debates come down to superficial nonsense. Yes, code quality matters. It’s critically important; it can make or wreck a company. Cosmetic differences, on the other hand, are just not that important or interesting. Tooling choices are important, but rarely as critical as opinionated engineers make them out to be, in the sense that they’re rarely existential matters for the company. Closed allocation is cultural death, and unethical management will ruin your startup, but the difference between Python and Scala is unlikely to be lethal. Can you write performant systems using mostly Python? Of course. Can high-quality, attractive code be written using an inelegant language like C++? Yes, it can. I have strong preferences regarding languages, but I’ve learned over the years not to take them too seriously. More dangerous than picking a suboptimal language is not getting any work done because of partisan bickering.

Language and tool wars are an outgrowth of a careerist idiocy that one would expect software engineers to be above. Engineers engage in this hyperbolic mudslinging because their career needs, in a typical corporate power struggle, often necessitate some control over the technical environment– and that’s often a zero-sum squabble. The software industry isn’t a real meritocracy, but it insists on looking like one, so the object of the game is to convince the team to use the tools with which one is most familiar, in order to become (because of tool fit, not intrinsic superiority) the most productive. This is the problem with technology in the late-autumn phase of a divergent spell: an engineer’s job performance is going to be more of a function of his match with the work environment and tools than of his overall competence, so there’s an enormous incentive to change the game if one can. There’s more individual gain in changing existing technical choices than grinding away at regular work. Most software engineers have learned this, and I can’t count on one hand the number of times I’ve seen a company go through a scorched-earth code rewrite because some douchebag managerial favorite only knew one language, and (of course) that language became the only possible option for the firm. This is terrible for the company that has to reinvent all of its technical assets, but beneficial to the favorite who naturally becomes the master of the new technical universe.

In a world of tight deadlines, short employment stints, and extremely detailed job requirements, this is only getting worse. It’s no longer acceptable to spend months in a “ramp up” period on a new job. It won’t get a person fired, but you’re unlikely to get the best projects if you don’t blow someone away in your first 3 months. So you need to find or carve out a niche where you can use tools you already know, in order to get some macroscopic achievement (a “launch”) as soon as possible. This forces companies into one of two undesirable alternatives. The first (sprawling divergence) is to let everyone use the tools they like, and the predictable result is “siloization” as engineers stick to the tools they already know how to use, rather than take the time to understand what other people are doing. Taking these systems into production and supporting them becomes a nightmare, because they often have 7 different NoSQL databases to support what’s essentially a CRUD app. The other (enforced convergence) is to require certain uniformity in development. The company becomes an “X Shop” for some specific language (or database, or methodology) X. That’s when the flame wars begin, because everyone is going to have an enormous stake in the choice of X. Now, it’s not enough for X to be the best tool for your project; you have to shove X down other peoples’ throats in the company, or you won’t be able to use it at all. This also falls down as necessity requires exceptions to the uniformity requirements, and the decision of who can get an exception becomes immensely political.

In truth, we as programmers are, in many companies, behaving like executives, spending more time arguing about how to do work than doing the actual work.

This, I think, is the fall-down calamity of the software industry. It’s why 50 percent of people who are professional programmers won’t be, seven years from now. Software engineering is all about improvement– building things that didn’t exist before, automating tedious processes– and it’s only natural that we want to improve ourselves. In order to get better, one needs a reliable stream of increasingly high-quality projects. What makes great software engineers extremely rare (and they are) isn’t a lack of talent alone; the limiting factor is the paucity of quality work. At a certain point, one reaches a level where it’s difficult to get quality work, even for a qualified (or overqualified) engineer. You end up spending more time convincing managers to give you good projects (playing politics, acquiring control of the division of labor) than you actually get to spend on the work. People get enervated and drop out, or they become managers and lose touch with the day-to-day process of writing code. Tooling wars are one component of this nasty slog that programmers have to enter in order to have a shot at the best work.

What’s the solution? I mentioned the alternative to uniformity, which is the “everyone uses whatever they want” divergent approach that often generates an intolerable support burden. It can work, but it will fail in the typical hierarchical corporation. When you have this proliferation of creativity and ideas, you need two things. First, there has to be a pruning process, because some of what is produced won’t be very good. Managers never get this right. Their decisions on what modules to keep (and, thereby, force engineers to maintain and use) and which ones to burn will be based on political factors rather than code or product quality. Second, it requires extremely strong cross-hierarchical communication, because it requires that people begin to make technical choices based on the long-term benefit of the group rather than short-term “productivity” in an attempt to acquire status. People who are building technical assets will need to actually give a damn about making their clients succeed, as opposed to the selfish, parochial goal of pleasing managers. You won’t get this kind of communication and pay-it-forward attitude– not as prevailing behaviors, rather than occasional serendipities endowed by the comfortable– in a closed-allocation company.

The open-allocation sociology is one in which there is cross-hierarchical collaboration because the conceptual hierarchy necessitated by the problem doesn’t congeal into a rigid hierarchy of people. Because there’s so much internal mobility, other teams are potential future teammates, and people will generally treat them well. What this means is that, while there will be divergence in the name of exploration and creative license, people will also take care of the convergence tasks, such as integrating their work with the rest of the company and teaching other teams how to use the assets they generate.

For a contrast, the closed-allocation sociology is one in which people strive, in the short term, for the image of superior productivity, in order to advance rapidly into a role where they control the division of labor instead of being controlled by it. This encourages people to diverge carelessly, for the twin purposes of (a) appearing highly productive and useful, and (b) creating personal security by generating technical assets that, although management can be convinced of their importance through political means, become so opaque to use as to leave other teams beholden to their creator. Of course, this productivity is illusory, the reality being that costs are externalized to the rest of the company. The heavy-handed, managerial antidote is to mandate convergence, but that inducing battles regarding which technologies and approaches live and which die. The result are hyperbolic, counterproductive and fear-driven arguments that devolve into the technical flame wars we all know and loathe.

As long as we have hierarchical corporations and closed-allocation regimes where one must either control the division of labor or be controlled by it, we will have endless flame wars over even the smallest of technical choices. The stakes are too high for them not to exist.

Lord Acton says: judge talent at its best and character at its worst. This is a wise principle, yet it fails us miserably when misapplied, as it often is in modern society. Why is that? The world is large, so our knowledge of each is extremely sparse. We often lack the information necessary to judge either talent or character well well. The consequence of information sparsity in judgment of talent is the existence of celebrity. It’s better to have everyone know that you’re a 6, than to be a 10 in secret. This itself is not so dangerous, but the contest for visibility, even in supposed meritocracies like the software industry, gets destructive quickly. Even in small companies, more effort is often expended to gain control of the division of labor (thus, one’s own visibility and reputation) than is spent actually completing the work. The fact that awful people are excellent at office politics is so well-known that it requires no documentation. It becomes visible within the first 6 months of one’s working life. This makes assessment of character as important as the judgment of skill and talent. Is the guy with the flashy resume a legitimate 99.99th-percentile talent, or a degenerate politicker and credit-taker who managed to acquire credibility? Reference checking is supposed to solve that, and it doesn’t work. I’ll get to that, a little bit later.

Information sparsity in the assessment of talent is a known danger, but I tend to see it as a short-term and minor threat. There’s probably an eventual consistency to it. Over time, people should converge to levels of challenge, responsibility, and influence commensurate with their ability. More dangerous, and infinitely more intractable, is the information sparsity that pertains to character. People tend to overestimate, by far, their ability to judge other peoples’ ethical mettle. In fact, the vast majority of them are easy to hack, and their excessive confidence in their own assessment is, in truth, easily used against them by the bad actors.

This problem is pretty much impossible to solve. Most people know from experience that the worst people– the psychopaths– are superficially charming, which means that personal impressions are of low value. What about getting access to the person’s history? In employment, that’s what reference checks are for, but shady characters often have great references. Why? Because they lie, extort, and manipulate people until their histories become not only socially acceptable but outright attractive. They hack people with as much skill and malice as the worst black-hat “crackers”. The people who are harmed by intensive reference checks are honest people with difficult histories, not the degenerate and dishonest who are the real threat.

My experience is that people lack the tools to judge others for character, at least at scale. Any fair punitive structure is predictable, and the most skilled of the bad actors will adapt. Any unpredictable punitive structure will be unfair, and rely on decisions made by influential humans, who are more likely than average to be psychopaths, and will certainly have psychopathic courtiers (whom the powerful person has not yet detected). The best one can do is to judge people by their actions, and to punish bad deeds swiftly and objectively. This is not a trivial art, of course.

Laws and imprisonment serve this punitive purpose, but most of the people in our jails are impulsive people of low social class, with only moderate overlap between the imprisoned population and the psychopaths. In employment, there’s a naive hope that, while psychopaths can climb high within corporations, they will eventually be unable to escape their histories and be flushed out of respectable careers. It never happens that way. Moral degenerates don’t get blacklisted. They acquire power and do the blacklisting.

One acquired strategy for dealing with such people is “Distrust everyone”. That’s how most seasoned managers and executives, having been robbed a couple times by dishonest subordinates, tend to view the people below them– with implicit, prevailing distrust. That strategy fails especially badly. Why? First, there are degrees of trust and distrust. Becoming a managerial favorite (managers are not always psychopaths, but managerial favorites almost always are) simply requires superiority in relative trust, not any level of absolute trust. Second, it’s functionally impossible to get a complex job done (much less lead a team) with prevailing total distrust of everyone, so people who “distrust everyone” are desperate for people they can give partial trust. Psychopaths play people with that attitude quite easily. It’s not even work for them. A boss who thinks his subordinates are all morons is surprisingly easy to hack.

The conclusion of all this is that, in defending scalable institutions such as corporations against psychopaths, we’re basically helpless. We don’t have the tools to detect them based on affability or social proof, and any strategy that we devise to deal with them, they will subvert to their own ends. We can’t “beat” them when they look exactly like us and will be undetected until it’s too late. Our best shot is not to attract them, and to avoid engaging in behaviors that make our institutions and patterns most easily hackable.

Despite our complete lack of ability to assess individuals for character at scale, we develop metrics for doing so that often not only fail us, but become tools of the psychopath. A going assumption that people make is that the small is indicative of the large. If Fairbanks is chilly in the summer, it must be frigid in the winter. (This applies to most climates, but not to San Francisco.) People who make occasional misspellings in email must be stupid. People who have mediocre accomplishments (by adult standards) at young ages are destined for adult brilliance. People who regularly take 75-minute lunches are “time-stealing” thieves.

Talent is judged in the workplace based on minor accomplishments, largely because there are so few opportunities for major accomplishment, and those are only available to the well-established. The guy who reliably hits a “6″ is judged to be capable of the “9″ (see: Peter Principle) while the one who gets bored and starts dropping “5″s is flushed out. Character is judged, similarly, based on useless and minor signals. The person who regularly arrives at 9:00, never says the wrong thing, and projects the image of a “team player” (whatever the fuck that means) gets ahead. What takes the place of character– which, I contend, cannot be assessed at scale and amid the extreme information sparsity of modern society– is superficial reliability. The people who pass what a company thinks are character and “culture fit” assessments are, rather than those of pristine character, the superficially reliable.

Who wins at this game? I wouldn’t say that it’s only psychopaths who win, but the best are going to be the psychopaths. The earnestly honest will break rules (formal and informal) to get work done. They care more about doing the right thing than being perceived the right way. Psychopaths are not by-the-word rule-followers with regard to formal policies, but they always follow the informal social rules (even to the breach of formal and less-powerful informal rules). They figure them out the quickest, have few distractions (since they rarely do actual work; that’s not what the office game is about!) and, fairly early on, find themselves in the position to make those rules. 

Superficial reliability works in favor of the worst people. Why? It evolves into a competition. Once everyone is in the office from 9:00 to 6:00, the new standard becomes 8:00 to 7:00. Then it’s 7:00 to 8:00, with expected email checking to 11:00. People start to fail. The noncompliant are the first to drop away and judged by the organism (the team, management) to have been the least dedicated, so it’s not seen as a loss. The next wave of failures are the enervated compliant, who meet the increasingly difficult standards but underperform in other ways. They spend their 13 hours at the office, but start making mistakes. They turn into temporary incompetents, and are flushed out as well. They’re not seen as a loss either. “We have a tough culture here.” As those burn off, people who were formerly at the center of the bell curve (in reliability, status, and performance) are now on the fringe, which means that there’s an atypically large set of people on the bubble, generating a culture of anxiety. They become catty and cutthroat now that the middle is no longer a safe place to be. People fight, and some come out of it looking so terrible that their reputations are ruined. They leave. Psychopaths rarely enter these contests directly, but evolve into puppet masters and arms dealers, ensuring that they win regardless of each battle’s outcome. Soon, the psychopath has entrenched himself as a key player in the organization. He’s not doing most of the work, but he’s feared by the actual stars, enough that they’ll let him take credit for their work and (in management’s eye) become one.

Most reliability contests work this way. There’s some performance metric where the bottom few percent justly deserve to be fired. As a limited measure, such a “sweep” is not a bad idea. (“Let’s stop paying the people who never show up.”) Management, however, is not measured or limited. It’s faddish, impulsive, absolute, and excessive. Whatever policy is used to separate from true underperformers (about 2%) must also be used to “stack rank” the other 98 percent. It’s no longer enough to enforce an honest 8-hour day; we must require an 11-hour day. This overkill damages the work environment and culture, and psychopaths thrive in damaged, opaque, and miserable environments.

Another example is reference checking in employment. The real purpose of the reference check is to discourage the morally average from lying about their histories, and it works. The moral “middle man” at the center of the ethical bell curve would probably lie on his resume given the right incentives, but would stop short of asking 3 friends to support the lie by posing as peers at jobs the person did not hold. Most people won’t make that kind of demand of people who aren’t close to them, but few people want to be seen as unethical by close colleagues. That is the point where the average person says, “Wait a minute, this might be wrong.” The classic, three-reference check also filters out the honest but undesirable candidates who just can’t find three people to recommend their work. It’s a reliability test, in that anyone who can’t find 3 people in his last 5 years to say good things about him is probably in that bottom 2% who are undesirable hires for that reasonl alone. Yet, at senior ranks in large companies, reference checking becomes a reliability contest, with 10 to 20 references– including “back channel” references not furnished by the candidate– being required. At that point, you’re selecting in favor of psychopaths. Why? Most honest people, playing fair, can’t come up with 20 references, nor have they engaged in the intimidation and extortion necessary to pass an intensive “back-channel” reference check in a world where even a modestly positive reference means no-hire. It’s those honest people who fail those cavity searches. A psychopath with no qualms about dishonesty and extortion can furnish 50 references. Beyond the “classic 3″, reference checking actually selects for psychopathy. 

Why do psychopaths never fail out, even of reliability contests designed to cull those of low character? The answer is that they have a limited emotional spectrum, and don’t feel most varieties of emotional pain, which makes them exceptionally good at such contests. They don’t become upset with themselves when they produce shoddy work– instead, they plan a blame strategy– so they don’t mind 15-hour days. (Office politics is a game for them, and one they love to play, so long hours don’t bother them.) They are emotionally immune to criticism as well. While they care immensely about their status and image, they have no reason to fear being dressed down by people they respect– because they don’t actually respect anyone. While psychopaths seem to despise losing, given the awful things they will do to avoid a minimal loss, even defeat doesn’t faze them for long. (This is an erroneous perception of the psychopaths; when we see psychopaths doing awful things to avoid minor losses, we assume they must have a desperate hatred of losing because we would require extreme circumstances in order to do such bad things. In truth, the difference is that they have no internal resistance against bad action.) Losses do not depress or hamper them. They pop right back up. Psychopaths are unbeatable. You can’t find them out until it’s too late, and whatever you try to kill them with is just as likely to hit someone innocent. Indeed, they thrive on our efforts to defeat them. When they are finally caught and prone, our punishments are often useless. There is truly “no there there” to a psychopath, and they have nothing to lose.

For an aside, I am not saying that we are powerless to curtail, punish, or rehabilitate the larger category of “bad actors”. Laws, social norms, and traditional incentives work well for normal people. Petty theft, for example, is rare because it is punished. Plenty of non-psychopaths would– out of weakness, desperation, curiosity, or even boredom– steal if they could get away with it. Jail time deters them. Prison is an environment to which normal people adapt poorly, and therefore an undesirable place to be. Psychopaths are different in many ways, one of which is that they are extremely adaptive. They love environments that others cannot stand, including prisons and “tough” workplace cultures. Punishing a psychopath is very hard, given his imperviousness to emotional pain. You could inflict physical pain or even kill him, but there would be no point. He would suffer, but he would not change.

Why does psychopathy exist? It’s useful to answer this question in order to best understand what psychopathy is. My best guess at it is that it has emerged out of the tension between two reproductive pressures– r- and K-selection– that existed in our evolutionary environment. An r-selective strategy is one that maximizes gross reproductive yield, or “spray and pray”. K-selective strategies are focused more on quality– fewer, more successful, offspring. The r-selective “alpha” male has a harem of 20 women and 200 children, most neglected and unhealthy. The K-selective “beta” has one wife and “only” 8 or 9 offspring, and invests heavily in their health. Neither is innately superior to the other; r-selective strategies repopulate quickly after a crisis, while K-selective quality-focused strategies perform well in stability. Human civilization has been the gradual process of the K-strategist “betas” taking over, first with monogamy and expected paternal investment, which was later extended to political and economic equality (because high-quality offspring will fare better in a stable and just world than a damaged one). Almost certainly, all humans possess a mix of “alpha” and “beta” genes and carry impulses from both evolutionary patterns, with the more civilized beta strategy winning over time, but not without a fight. Indeed, what we view as morally “good” in many societies is intimately connected with beta patterns– sexual restraint, nonviolence, positive-sum gradualism– while our concept of “sin” is tied to our alpha heritage. Psychopathy seems to be an adaptation in which the beta, or K-selective, tendencies of the mind are not expressed, allowing the alpha to run unchecked. In evolutionary terms, this made the individual more fit, although often at the expense of society.

Psychopaths (for obvious evolutionary reasons) like sex, status, and resources, but that alone doesn’t identify them, since almost everyone does. What differentiates the psychopath is the extreme present-time orientation, as well as the willingness to make ethical compromises to get them. The future-oriented, positive-sum mentality is absent in the psychopath. Unhampered by conscience, psychopaths quickly acquire resources and power, these being key (at least, throughout most of our evolutionary history) to reproductive proliferation. In business, their sexual appetites are not of major interest. What’s most relevant to our problem is their attraction to power and status. That is what they want. It’s only about money for them so far as it confers social status.

If we cannot defeat psychopaths, then what should we do? This turns out not to be a new problem– not in the least. Why, for example, do American elected officials draw such mediocre salaries? Why do we need all the checks and balances that make even the presidency so much damn work? Making power less attractive is one of the first principles of rational government, as the concept was developed during the Age of Reason. The reactionary clergies and hereditary aristocracies had to go– that much was clear– but how could one prevent a worse and more brutal lord from filling the vacuum? The idea was to compensate for power’s natural attractiveness by limiting it and attaching responsibilities. In the U.S., this even came to the matter of location, with the nation’s capital being chosen deliberately in an undesirable climate. In elected politics, I would say that this has mostly worked. We’ve had some downright awful political leaders, but a surprisingly low number (by corporate comparison) of psychopaths in top political positions. I wouldn’t go so far as to say that elected office doesn’t attract them, but other positions of power attract them much more. With the first-rate psychopaths making millions in the corporate world, the psychopaths who are attracted to elected political positions are the C-students in psychopath school.

Taking a macroscopic perspective, psychopathy is a very hard problem to solve. A closed system such as a nation-state has some probably invariant population of psychopaths that, inevitably, will be attracted to some variety of social status and dominance over other people. Flush them out of politics, and they end up in business. Yet if business were made unattractive due to an overpowered state (e.g. left-wing authoritarianism) they would end up back in government. They have to go somewhere, and it is impossible to identify them until they’ve done their damage (and, often, not even then). Yet the microeconomic problem for an individual firm is much easier– don’t attract psychopaths.

In technology, one strategy is Valve-style open allocation, under which employees are permitted to work for the firm directly rather than requiring managerial approval. Want to change projects? Move your desk and start. The typical extortion that middle managers use to build their careers– work for me or you don’t work here at all– doesn’t exist, because no one has that authority. Managerial authority attracts psychopaths like little else– more than money or prestige– and if one can do without it, one should consider doing so.

Much of the appeal of startups in technology is the perception (sometimes, an inaccurate one) that small technology companies haven’t yet been corroded and politicized by managerial extortions. In the ideal case, a startup operates under a constrained open allocation. It’s not yet “work on whatever you want”, because the startup requires intense focus on solving a specific problem, but employees are trusted to manage their own contribution. When do those companies go to closed allocation? Often, “hot” companies lose their cultural integrity in the process of hiring executives. The flashy career office-politician with impressive titles and “a track record” demands authority from the go, and it’s given to him. Five direct reports is not enough; he demands ten. He gets 15. Over time, employees lose status and autonomy as it’s chipped away to feed these people.

Most of the cultural losses that companies endure as they grow are suffered in the quest to hire executives from the outside, but what kind of person are you going to attract if you’re immediately willing to sell off your employees’ autonomy to “close a deal”? The people you’re most likely to get are those who enjoy power over people. Not all of these are psychopaths (some are mere narcissists or control freaks) but many are. Your culture will disappear rapidly.

If you’re running a typical VC-funded, build-to-flip operation, then hiring power-hungry external executives might be the way to go. A great way to buy an important decision-maker (an investor, an executive at an acquirer) is to give his underperforming friend an executive position at your company. You might take on a psychopath or few, but you’re not going to be in the company for very long, so it’s not your concern. On the other hand, if you want to build a stable company whose culture and values will still be worth a damn in 20 years, then you can’t do that. To the extent that your organization needs positions of power to function, you need to make them undesirable to the psychopath. This is one of the major reasons why you need intrinsic limits (checks and balances) on power.

Unfortunately for corporate executives, making a company less psychopath-friendly means equalizing the distribution of power and reward within companies. It means moving away from the CEO-as-king model and the eight-figure pay packages. Over the past forty years, we’ve been paying more and getting less when it comes to corporate management. Flushing out the psychopaths requires that we pay less, both financially and in terms of authority over other people, for managerial positions. The whole concept of what it means to be an “executive” will require reinvention as radical as the replacement of hereditary monarchs by elected legislators.

The stupid, superficial reliability contests that corporations use to assess character and protect themselves against psychopaths don’t work. In fact, they do the opposite, becoming the psychopath’s favorite tools. Companies that want to avoid being invaded and controlled by such people will have to reinvent themselves in a form radically unlike the traditional, hierarchical corporation.